I have to say something. After reading through this thread I am very concerned for the safety of the lady described in the author's posts. In my opinion it's not about alcoholism. It's about a man's obsession with a woman he has known for a very short amount of time.
Deadboy: a lot of your language concerns me, such as: "tonight she's going to hit the wine, let's make a bet" or "when she's sober she's perfect. She does anything I want," or "she will be drunk tonight.....anyone want to wager a bet???" NO. You're betting on her failures, you're policing her activities, looking through her personal items, driving to her place unexpected, asking for past boyfriend's phone numbers (I wouldn't give you an ex boyfriend's number either), keeping a journal/log on her activities, etc. You're building yourself up as some kind of victim even though it's obvious (after reading the entire thread) that you have flung yourself into this role 100% after 2 months. She's 35 years old and you're thinking of speaking to her parents?! All those e-mails you have written her and meetings you'regoing to. It appears to me that you're the one who is out of control. You're crossing so many boundaries here, this could easily turn into you stalking her in the future. She is going to get sick of being controlled after only knowing you a couple months and will hopefully stop taking your calls and block your e-mails. If she was a friend of mine I would advise her that. You're taking over her life in a very creepy and all consuming way. She would be right to cut you off as you are violating her right to privacy as a human being.
Bottom line is I hope one of you walks away from this "relationship" (if you can call it that) for the safety of each of you individualy. I believe she will be the one to do it though and I hope you will be able to let her go.
I also think that all advisors need to be careful and keep in mind the woman's safety and the author's state of mind.